# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014


data_cu_dm12452_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5200(2)
_cell_length_b                   5.8727(2)
_cell_length_c                   16.9410(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.145(2)
_cell_angle_gamma                90.00
_cell_volume                     839.10(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4577
_cell_measurement_theta_min      5.24
_cell_measurement_theta_max      68.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8656
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.24
_diffrn_reflns_theta_max         69.93
_reflns_number_total             2875
_reflns_number_gt                2755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2875
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.97532(13) 0.2597(2) 0.74200(6) 0.0263(3) Uani 1 1 d . . .
C1 C 0.94017(18) 0.0721(3) 0.69357(8) 0.0319(3) Uani 1 1 d . . .
H1 H 0.8402 0.0441 0.6625 0.038 Uiso 1 1 calc R . .
C2 C 1.06877(19) -0.0673(3) 0.69658(9) 0.0365(4) Uani 1 1 d . . .
H2 H 1.0747 -0.2057 0.6681 0.044 Uiso 1 1 calc R . .
C3 C 1.19265(17) 0.0341(3) 0.75052(8) 0.0325(3) Uani 1 1 d . . .
C4 C 1.35038(19) -0.0273(3) 0.77942(10) 0.0413(4) Uani 1 1 d . . .
H4 H 1.3942 -0.1655 0.7632 0.050 Uiso 1 1 calc R . .
C5 C 1.43908(18) 0.1179(4) 0.83164(10) 0.0456(5) Uani 1 1 d . . .
H5 H 1.5450 0.0777 0.8522 0.055 Uiso 1 1 calc R . .
C6 C 1.37711(18) 0.3228(4) 0.85516(9) 0.0421(4) Uani 1 1 d . . .
H6 H 1.4430 0.4205 0.8902 0.050 Uiso 1 1 calc R . .
C7 C 1.22274(16) 0.3878(3) 0.82897(8) 0.0334(4) Uani 1 1 d . . .
H7 H 1.1806 0.5269 0.8455 0.040 Uiso 1 1 calc R . .
C8 C 1.13176(15) 0.2385(3) 0.77692(8) 0.0278(3) Uani 1 1 d . . .
C9 C 0.87959(16) 0.2311(3) 0.89724(8) 0.0289(3) Uani 1 1 d . . .
H9 H 0.9277 0.1034 0.8759 0.035 Uiso 1 1 calc R . .
C10 C 0.84741(16) 0.2262(3) 0.97581(8) 0.0337(4) Uani 1 1 d . . .
H10 H 0.8740 0.0953 1.0079 0.040 Uiso 1 1 calc R . .
C11 C 0.77715(17) 0.4109(4) 1.00702(9) 0.0371(4) Uani 1 1 d . . .
H11 H 0.7550 0.4066 1.0604 0.045 Uiso 1 1 calc R . .
C12 C 0.73879(18) 0.6026(3) 0.96058(9) 0.0377(4) Uani 1 1 d . . .
H12 H 0.6904 0.7300 0.9819 0.045 Uiso 1 1 calc R . .
C13 C 0.77179(17) 0.6070(3) 0.88241(8) 0.0324(3) Uani 1 1 d . . .
H13 H 0.7462 0.7387 0.8506 0.039 Uiso 1 1 calc R . .
C14 C 0.84134(15) 0.4221(3) 0.85031(8) 0.0265(3) Uani 1 1 d . . .
C15 C 0.86522(15) 0.4336(3) 0.76229(8) 0.0265(3) Uani 1 1 d . . .
H15 H 0.9105 0.5863 0.7523 0.032 Uiso 1 1 calc R . .
C16 C 0.70538(15) 0.4141(3) 0.71189(8) 0.0276(3) Uani 1 1 d . . .
H16 H 0.6459 0.2790 0.7162 0.033 Uiso 1 1 calc R . .
C17 C 0.64259(17) 0.5739(3) 0.66193(8) 0.0292(3) Uani 1 1 d . . .
H17 H 0.7071 0.7024 0.6553 0.035 Uiso 1 1 calc R . .
C18 C 0.48217(17) 0.5720(3) 0.61549(8) 0.0284(3) Uani 1 1 d . . .
C19 C 0.37400(17) 0.4001(3) 0.62363(9) 0.0343(4) Uani 1 1 d . . .
H19 H 0.4026 0.2802 0.6605 0.041 Uiso 1 1 calc R . .
C20 C 0.22437(17) 0.4008(4) 0.57855(9) 0.0386(4) Uani 1 1 d . . .
H20 H 0.1516 0.2816 0.5845 0.046 Uiso 1 1 calc R . .
C21 C 0.18160(18) 0.5761(4) 0.52478(9) 0.0387(4) Uani 1 1 d . . .
H21 H 0.0797 0.5769 0.4937 0.046 Uiso 1 1 calc R . .
C22 C 0.28751(19) 0.7489(4) 0.51676(9) 0.0403(4) Uani 1 1 d . . .
H22 H 0.2581 0.8694 0.4803 0.048 Uiso 1 1 calc R . .
C23 C 0.43730(18) 0.7480(3) 0.56174(9) 0.0353(3) Uani 1 1 d . . .
H23 H 0.5095 0.8680 0.5558 0.042 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.381(2) . ?
N1 C8 1.3851(17) . ?
N1 C15 1.4604(19) . ?
C1 C2 1.363(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.425(2) . ?
C2 H2 0.9500 . ?
C3 C8 1.405(2) . ?
C3 C4 1.410(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C9 C14 1.387(2) . ?
C9 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.5349(17) . ?
C15 C16 1.5057(17) . ?
C15 H15 1.0000 . ?
C16 C17 1.324(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4773(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 C23 1.395(2) . ?
C19 C20 1.3902(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 107.26(13) . . ?
C1 N1 C15 127.25(11) . . ?
C8 N1 C15 125.01(12) . . ?
C2 C1 N1 110.58(13) . . ?
C2 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
C1 C2 C3 106.93(15) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C8 C3 C4 118.98(15) . . ?
C8 C3 C2 106.73(13) . . ?
C4 C3 C2 134.29(17) . . ?
C5 C4 C3 118.32(17) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.53(15) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.92(17) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 116.54(17) . . ?
C6 C7 H7 121.7 . . ?
C8 C7 H7 121.7 . . ?
N1 C8 C7 128.83(15) . . ?
N1 C8 C3 108.48(13) . . ?
C7 C8 C3 122.68(14) . . ?
C14 C9 C10 120.07(15) . . ?
C14 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.23(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.08(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.46(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.95(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 119.22(13) . . ?
C13 C14 C15 118.03(14) . . ?
C9 C14 C15 122.68(14) . . ?
N1 C15 C16 111.90(12) . . ?
N1 C15 C14 112.07(12) . . ?
C16 C15 C14 108.29(10) . . ?
N1 C15 H15 108.1 . . ?
C16 C15 H15 108.1 . . ?
C14 C15 H15 108.1 . . ?
C17 C16 C15 124.03(14) . . ?
C17 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C16 C17 C18 126.48(14) . . ?
C16 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
C19 C18 C23 118.68(13) . . ?
C19 C18 C17 122.02(13) . . ?
C23 C18 C17 119.30(14) . . ?
C18 C19 C20 120.92(15) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.83(16) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 119.75(13) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.43(16) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.39(16) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 0.02(15) . . . . ?
C15 N1 C1 C2 -172.24(13) . . . . ?
N1 C1 C2 C3 0.76(16) . . . . ?
C1 C2 C3 C8 -1.24(16) . . . . ?
C1 C2 C3 C4 178.84(15) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C5 178.99(16) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C1 N1 C8 C7 178.28(14) . . . . ?
C15 N1 C8 C7 -9.2(2) . . . . ?
C1 N1 C8 C3 -0.82(14) . . . . ?
C15 N1 C8 C3 171.66(12) . . . . ?
C6 C7 C8 N1 179.74(13) . . . . ?
C6 C7 C8 C3 -1.3(2) . . . . ?
C4 C3 C8 N1 -178.80(12) . . . . ?
C2 C3 C8 N1 1.27(15) . . . . ?
C4 C3 C8 C7 2.0(2) . . . . ?
C2 C3 C8 C7 -177.89(13) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C9 -0.5(2) . . . . ?
C12 C13 C14 C15 176.46(13) . . . . ?
C10 C9 C14 C13 0.2(2) . . . . ?
C10 C9 C14 C15 -176.61(13) . . . . ?
C1 N1 C15 C16 -10.64(19) . . . . ?
C8 N1 C15 C16 178.39(12) . . . . ?
C1 N1 C15 C14 111.24(15) . . . . ?
C8 N1 C15 C14 -59.74(17) . . . . ?
C13 C14 C15 N1 164.76(12) . . . . ?
C9 C14 C15 N1 -18.35(18) . . . . ?
C13 C14 C15 C16 -71.33(17) . . . . ?
C9 C14 C15 C16 105.56(15) . . . . ?
N1 C15 C16 C17 -117.16(16) . . . . ?
C14 C15 C16 C17 118.82(16) . . . . ?
C15 C16 C17 C18 -175.20(13) . . . . ?
C16 C17 C18 C19 3.8(2) . . . . ?
C16 C17 C18 C23 -176.25(15) . . . . ?
C23 C18 C19 C20 0.8(2) . . . . ?
C17 C18 C19 C20 -179.24(15) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C19 C18 C23 C22 -0.7(2) . . . . ?
C17 C18 C23 C22 179.36(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        69.93
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 979724'
